Albert rothmann



fat

Patented July 6, 1926.

UNITED STATES PATENT orr ca.

ALBERT nornmann, or HEIDELBERG, onaMAuY, assxenon r0 0. r. noanamenn. a

SCEENE G. M. B. H., OF MANNHEIM-WALDHOF, GERMANY.

mzarva'rrvns or mmossnzoxo'aorns.

I No Drawing. Application fled July 18, 1822, Serial no. 575,829, and inGermany July 20, 1981.

This invention relates to the preparation of derivatives ofortho-aminobenzoic acids which are designed to be used as remedies forgout and other maladies resulting from an excess-of uric acid in thehuman body.

I have found that a specially good reaction is obtained fromortho-aminobenzoic acid derivatives which are substituted in'the aminogroup by a quinoline-carboxylic acid radical.

Compounds of this kind can be prepared by the action ofquinoline-carboxylic acid chloride, or of derivatives or substitutionproducts of such, upon anthranilic acid. 1

It has been demonstrated by clinical experiments that the newcondensation products possess in an extraordinarily high degree thepower to eliminate uric acid from the system; they erful uric acidrinsing than the 2-phenylquinoline--carboxylic acid and derlvatives ofthe same hitherto known and generally used as a remedy for out. They,moreover, exhibit the valuable c aracteristics of being completelytasteless and of having no undesirable secondary effects as theirresult.

In the following example I have llustrated what I consider the bestmanner of carrying my invention into eflfect.

100 parts of 2-phen l-quinoline-i-carboxylic acid are suspen ed in 4:00parts of benzene, they are then treated with a solution of 112 parts ofthionyl-chloride in 200 arts of benzene and heated on the water bathfrom 3 to 4: hours with a reflux condenser. After distillin ofi thesolvent and the'excess of thionyl-c oride, the residue is dissolved in800 arts of hot benzene and a hot solution of parts of anthranilic acidin 400 parts of benzene is added, while powerfully stirring the mass.The reaction product is at once se arated out for .the most part. Thereaction mixture is heated a short time on the water bath, the depositbeing separated of! b3 suction after coo and be then drie It shows areddi yellow co or. I v

roduce a much more pow- .is obtained in the form M.P.226-227,O.

For the further urification the reaction product is suspen ed in water,heated a short time and thereupon filtered oil. This easily soluble inwarm benzene, in chloroform and acetic ester. Recr stallized fromalcohol the new compound aving the following composition coon / I claimas my invention: s

1, As a new chemical compound, an ortho-. amino-benzoic acid havingsubstituted in the amino-group a compiound comprising a quinolinecarboxylic aci radical, such compound being solid, tasteless and havingthe property of rinsing uric acid from the body.

2. As a new chemical compound, an anthranilic acid derivative in whichthe res dueof an aryl-quinoline carboxylic acid is substituted in theamino-group corresponds to the formula:

CO-HN 1 and which of fine needles of such compound being insoluble inwarm water, tasteless, and possessing the property of rinsing uric acidfrom the system.

3. As a new Composition of matter, anthranilic acid substituted in theaminogroup by the residue of 2-phenylquinolin-4- carboxylic acid, thissubstance. being insoluble in hot water, readily soluble in warmbenzene, in chloroform and in acetic ester and, when recrystallized fromalcohol, forming fine needles having a melting point of 226-227,centigrade, and whose constitution is expressed by the formula:

signature.

COOK

. 2 CO.HN 1

ALBERT ROTHMANN.

